AR040970A1 - METHOD FOR THE SEPARATION OF INTERMEDIARIES THAT CAN BE USED FOR THE PREPARATION OF SCITALOPRAM - Google Patents

METHOD FOR THE SEPARATION OF INTERMEDIARIES THAT CAN BE USED FOR THE PREPARATION OF SCITALOPRAM

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Publication number
AR040970A1
AR040970A1 ARP030102904A ARP030102904A AR040970A1 AR 040970 A1 AR040970 A1 AR 040970A1 AR P030102904 A ARP030102904 A AR P030102904A AR P030102904 A ARP030102904 A AR P030102904A AR 040970 A1 AR040970 A1 AR 040970A1
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AR
Argentina
Prior art keywords
formula
alkyl
amino
hal
halogen
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ARP030102904A
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Spanish (es)
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Lundbeck & Co As H
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Publication of AR040970A1 publication Critical patent/AR040970A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/001—Amines; Imines
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/002—Nitriles (-CN)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/008—Preparation of nitrogen-containing organic compounds containing a N-O bond, e.g. nitro (-NO2), nitroso (-NO)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
    • C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Reivindicación 1: Un método para la preparación del enantiómero R o S de un diol que tiene la fórmula (1) donde R es ciano o un grupo que puede convertirse a un grupo ciano, Z es un grupo -CH2-N(R´ R") donde R´ y R" son alquilo C1-6 o R´ y R" están conectados entre sí para formar una estructura cíclica incluyendo el átomo N al cual están unido, o Z es un grupo que puede convertirse a un grupo dimetilaminometilo, la línea punteada representa un enlace doble o simple y Hal es halógeno o una sal del mismo, y/o el enantiómero opuesto de un diol acilado que tiene la fórmula (2), donde R, Z, la línea punteada y Hal son tal como se definieron anteriormente, W es O o S, y R3 es -Y-R1, donde R1 es alquilo C1-10, alquenilo C2-10 o alquinilo C2-10 todos los cuales pueden estar opcionalmente sustituidos una o más veces con sustituyentes seleccionados a partir de alcoxi C1-10, alquiltio C1-10, hidroxi, halógeno, amino, nitro, ciano, alquilamino C1-10, di-(alquil C1-10)amino, arilo, ariloxi, ariltio y heteroarilo, o R1 es arilo, en donde cualquiera de los grupos arilo y heteroarilo pueden estar opcionalmente sustituidos una o más veces con sustituyentes seleccionados a partir de alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcoxi C1-10, alquiltio C1-10, hidroxi, halógeno, amino, nitro, ciano, alquilamino C1-10 y di-(alquil C1-10)amino e Y es un enlace, O, S o NH, o una sal del mismo, que comprende: a) someter un compuesto racémico de fórmula (3) donde R, Z, la línea punteada y Hal son tal como se definieron anteriormente, para la acilación enzimática selectiva utilizando un agente acilante que tiene la fórmula (4), o (5), o (6) o un isocianato que tiene la fórmula R1-N=C=O o un isocianato que tiene la fórmula R1-N=C=S; donde X es O o S; W es O o S; U es O o S, V es halógeno; R0 es alquilo C1-10, alquenilo C2-10 o alquinilo C2-10 todos los cuales pueden estar opcionalmente sustituidos una o más veces con sustituyentes seleccionados a partir de alcoxi C1-10, alquiltio C1-10, hidroxi, halógeno, amino, nitro, ciano, alquilamino C1-10, di-(alquil C1-10)amino, arilo, ariloxi, ariltio y heteroarilo, o R0 es arilo, donde cualquiera de los grupos arilo y heteroarilo pueden estar opcionalmente sustituidos una o más veces con sustituyentes seleccionados a partir de alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcoxi C1-10, alquiltio C1-10,hidroxi, halógeno, amino, nitro, ciano, alquilamino C1-10 y di-(alquil C1-10)amino; R1 es como se definió para R0; R2 es como se definió para R0, o R2 es un grupo saliente apropiado; o R0 y R1 juntos forman una cadena de 3 a 5 átomos de C; siempre que W y U no sean S cuando X es S; para formar una mezcla del material de partida de la fórmula (1) en cualquier forma R o S y el enantiómero opuesto de un compuesto que tiene la fórmula (2) en donde R, W, Hal, R3, la línea punteada y Z son como se definieron anteriormente; o b) someter un compuesto racémico de fórmula (2) en donde R, Z, W, Hal la línea punteada y R3 son como se definieron anteriormente, para desacilación enzimático selectiva para formar una mezcla de un compuesto deacilado de fórmula (1) en donde R, Hal, la línea punteada y Z son como se definieron anteriormente en cualquier forma R o S y el material de partida acilado de la fórmula (2) en la forma del enantiómero opuesto, opcionalmente seguido de, en cualquier orden, aislamiento del enantiómero S o R del compuesto de fórmula (1) y/o el enantiómero opuesto del compuesto de fórmula (2) o una sal del mismo.Claim 1: A method for the preparation of the R or S enantiomer of a diol having the formula (1) wherein R is cyano or a group that can be converted to a cyano group, Z is a -CH2-N group (R 'R ") where R 'and R" are C1-6 alkyl or R' and R "are connected to each other to form a cyclic structure including the N atom to which they are attached, or Z is a group that can be converted to a dimethylaminomethyl group, the dotted line represents a double or single bond and Hal is halogen or a salt thereof, and / or the opposite enantiomer of an acylated diol having the formula (2), where R, Z, the dotted line and Hal are as defined above, W is O or S, and R3 is -Y-R1, where R1 is C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl all of which may be optionally substituted one or more times with substituents selected from from C1-10 alkoxy, C1-10 alkylthio, hydroxy, halogen, amino, nitro, cyano, C1-10 alkylamino, di- (C1-10 alkyl) amino, ari lo, aryloxy, arylthio and heteroaryl, or R1 is aryl, wherein any of the aryl and heteroaryl groups may be optionally substituted one or more times with substituents selected from C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl , C1-10 alkoxy, C1-10 alkylthio, hydroxy, halogen, amino, nitro, cyano, C1-10 alkylamino and di- (C1-10 alkyl) amino and Y is a bond, O, S or NH, or a salt thereof, which comprises: a) submitting a racemic compound of formula (3) where R, Z, the dotted line and Hal are as defined above, for selective enzymatic acylation using an acylating agent having the formula (4) , or (5), or (6) or an isocyanate having the formula R1-N = C = O or an isocyanate having the formula R1-N = C = S; where X is O or S; W is O or S; U is O or S, V is halogen; R0 is C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl all of which may be optionally substituted one or more times with substituents selected from C1-10 alkoxy, C1-10 alkylthio, hydroxy, halogen, amino, nitro , cyano, C1-10 alkylamino, di- (C1-10 alkyl) amino, aryl, aryloxy, arylthio and heteroaryl, or R0 is aryl, where any of the aryl and heteroaryl groups may be optionally substituted one or more times with selected substituents from C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C1-10 alkoxy, C1-10 alkylthio, hydroxy, halogen, amino, nitro, cyano, C1-10 alkylamino and di- (C1-10 alkyl )Not me; R1 is as defined for R0; R2 is as defined for R0, or R2 is an appropriate leaving group; or R0 and R1 together form a chain of 3 to 5 C atoms; provided that W and U are not S when X is S; to form a mixture of the starting material of the formula (1) in any R or S form and the opposite enantiomer of a compound having the formula (2) wherein R, W, Hal, R3, the dotted line and Z are as defined above; or b) subjecting a racemic compound of formula (2) wherein R, Z, W, Hal the dotted line and R3 are as defined above, for selective enzymatic deacylation to form a mixture of a deacylated compound of formula (1) wherein R, Hal, the dotted line and Z are as defined above in any form R or S and the acylated starting material of the formula (2) in the form of the opposite enantiomer, optionally followed by, in any order, isolation of the enantiomer S or R of the compound of formula (1) and / or the opposite enantiomer of the compound of formula (2) or a salt thereof.

ARP030102904A 2002-08-12 2003-08-11 METHOD FOR THE SEPARATION OF INTERMEDIARIES THAT CAN BE USED FOR THE PREPARATION OF SCITALOPRAM AR040970A1 (en)

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DKPA200201201 2002-08-12

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AR040970A1 true AR040970A1 (en) 2005-04-27

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US (2) US20070129561A1 (en)
EP (2) EP1534654A1 (en)
JP (3) JP4694837B2 (en)
KR (1) KR20050053618A (en)
CN (2) CN101045664B (en)
AR (1) AR040970A1 (en)
AU (1) AU2003250321B2 (en)
BR (1) BR0313114A (en)
CA (1) CA2495118C (en)
EA (1) EA011762B1 (en)
HK (2) HK1083828A1 (en)
IL (1) IL166319A0 (en)
IS (1) IS7642A (en)
ME (1) ME00028B (en)
MX (1) MXPA05001400A (en)
NO (1) NO20051292L (en)
NZ (1) NZ537785A (en)
PE (1) PE20040991A1 (en)
PL (1) PL374835A1 (en)
RS (1) RS20050092A (en)
TW (1) TWI306846B (en)
UA (1) UA78840C2 (en)
WO (1) WO2004014821A1 (en)
ZA (1) ZA200500728B (en)

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CN1510024A (en) * 2002-12-24 2004-07-07 北京德众万全药物技术开发有限公司 Compound for preparing citalopram enantiomer and its production

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